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Solvent hydrogen bonding and structural effects on nucleophilic substitution reactions: Part 3. Reaction of benzenesulfonyl chloride with anilines in benzene/propan-2-ol mixtures

✍ Scribed by D. S. Bhuvaneshwari; K. P. Elango

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
212 KB
Volume
39
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

Substitution reactions of 13 para‐ and meta‐substituted anilines with benzenesulfonyl chloride in varying mole fractions of benzene in propan‐2‐ol have been investigated conductometrically. The second‐order rate constants correlate well with pK~a~ values of anilines and with the Hammett's equation. The negative Hammett reaction constant indicates the formation of an electron‐deficient transition state. The rate data correlate satisfactorily with macroscopic solvent parameters such as relative permittivity, ε~r~, and polarity, E~T~^N^. Correlation of rate data with Kamlet–Taft solvatochromic parameters (α, β, π*) suggests that both the specific and nonspecific solute–solvent interactions influence the reactivity. © 2007 Wiley Periodicals, Inc. Int J Chem Kinet 39: 657–663, 2007

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